DoubleClick Dude Aces His Second Act

Mr. Ryan first saw the potential of the Internet in … the Dilbert Zone. In 1995, Mr. Ryan was working as senior vice president of business and finance at United Media when he launched Dilbert.com, an online hub for comic strips about the rotund office worker with Office Space-like musings. It would become the most popular and profitable comic-strip site on the Web. “We started to realize we had this very successful advertising-supported, commerce-enabled Web site,” Mr. Ryan explained. “I thought, this is the most fundamental business trend I’m going to see in my lifetime. … We had tens of thousands of people coming to the site [that utilized] all the things that are great about the Internet. We can sell things. This is going to happen all across the industry. It’ll happen for information, news, everything. So I’m going to start a company.”

And that company turned out to be DoubleClick. Mr. Ryan was looking to start an online advertising company similar to DoubleClick, which was founded by Mr. Merriman and Kevin O’Connor. But he decided to join their team as chief financial officer when he realized they would crush the competition. DoubleClick was one of the first tech companies to build its reputation in New York; it was successful because of its proximity to Madison Avenue and its big-name clients, including Coca-Cola, Motorola, L’Oreal, Visa and Microsoft. In 1996, Mr. Ryan took over Mr. O’Connor’s day-to-day duties as CEO and faced the challenge of rebuilding the company after Wall Street crumbled under the Internet bubble burst in 2000.

“I spent the next three years really downsizing the company,” Mr. Ryan said. He cut his staff in half and rearranged management. “It’s especially hard because two years ago, you couldn’t imagine what it was like to work at DoubleClick, because everyone seems like a genius, you think the CEO’s a genius, everything is going well. And then everything comes crashing down.” They watched companies drop from their client list on a daily basis.

But Mr. Ryan started crunching the numbers. Seventy percent of their clients went under. However, 80 percent of their competitors fell off, too. “We picked up an equivalent of 30 or 40 percent of the business from them,” he explained. They cut their costs in half and earned 70 percent of their previous revenues. “You do that math, and all of a sudden, we came out, by 2004, with this enormously profitable company that had a hugely dominant position in what we did.” Even during hopeless times, Mr. Ryan and DoubleClick had good numbers.

The company also provided fertile ground for young New Yorkers to build their tech expertise and move on to sprout other businesses and snag other jobs in the city. “The thing I feel best about actually is that more companies in New York are willing to hire DoubleClick people than almost any company. A lot of the people [on the Silicon Alley 100] worked at DoubleClick. My CFO is now the CFO of Oracle. My head of HR is now HR for Cisco. So we get people who can clearly work at a company many times the size of us.”

It should be no surprise that Mr. Ryan is an evangelist for the New York tech community.

Despite the current economic slowdown, he thinks the city’s tech community will do just fine, simply because it’s New York.

“Obviously, we’re going into a downturn, so everyone’s going to get hurt. That goes without saying,” he said. “But New York, when you think of the Internet sector, the ad industry is here and will continue to be here, and that’s a big advantage. The fashion industry is here, and will continue to be here. Wall Street, same thing. Music industry, split between here and L.A. The Internet sector is here to stay.” Sounds like Mr. Ryan and AlleyCorp are, too.